methyl (1S,4aS,5R,7R,7aS)-7-(acetyloxymethyl)-5,7-dihydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 173f7ca1-af1a-457c-935e-96dc2b352c0e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5R,7R,7aS)-7-(acetyloxymethyl)-5,7-dihydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC(=O)OCC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C19H28O13/c1-7(21)30-6-19(27)3-9(22)11-8(16(26)28-2)5-29-17(12(11)19)32-18-15(25)14(24)13(23)10(4-20)31-18/h5,9-15,17-18,20,22-25,27H,3-4,6H2,1-2H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s1
• InChI Key: WKNQJIJVUGESJH-NGQYDJQZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₁₃
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.15299094 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.49
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6184	61.84%
Caco-2	-	0.8514	85.14%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6333	63.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7767	77.67%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8153	81.53%
P-glycoprotein inhibitior	-	0.7697	76.97%
P-glycoprotein substrate	-	0.6244	62.44%
CYP3A4 substrate	+	0.6540	65.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.9540	95.40%
CYP2C9 inhibition	-	0.9285	92.85%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9180	91.80%
CYP1A2 inhibition	-	0.9127	91.27%
CYP2C8 inhibition	-	0.6223	62.23%
CYP inhibitory promiscuity	-	0.9240	92.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6956	69.56%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9483	94.83%
Skin irritation	-	0.7219	72.19%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	+	0.5163	51.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4857	48.57%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.8574	85.74%
skin sensitisation	-	0.8621	86.21%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7719	77.19%
Acute Oral Toxicity (c)	III	0.4102	41.02%
Estrogen receptor binding	+	0.7123	71.23%
Androgen receptor binding	+	0.5243	52.43%
Thyroid receptor binding	-	0.6033	60.33%
Glucocorticoid receptor binding	-	0.5786	57.86%
Aromatase binding	+	0.5985	59.85%
PPAR gamma	+	0.5190	51.90%
Honey bee toxicity	-	0.7857	78.57%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4174	41.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.49%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.51%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.37%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.92%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.13%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.83%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.89%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.81%	97.09%
CHEMBL5028	O14672	ADAM10	83.10%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.08%	90.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.74%	96.61%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.47%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.43%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	82.21%	92.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	80.49%	91.65%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.47%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.45%	95.50%

Plants that contains it

• Fouquieria diguetii

Cross-Links

• PubChem: 162926534
• LOTUS: LTS0254082
• wikiData: Q105307497